STUDIES IN THE WAGNER-MEERWEIN REARRANGEMENT. PART I

Abstract

The preparation by a convenient route of 9-methyl, ethyl, isopropyl, l-butyl, and benzyl phenanthrenes is described. This consists of the alkylation of methyl fluorene-9-carboxylate under mild conditions, reduction of the ester group with lithium aluminum hydride, and then tosylation of the carbinol. The tosyl esters so prepared rearrange to alkylphenanthrenes with simultaneous loss of the elements of toluenesulphonic acid, when heated alone or in formic acid. Dehydration of the carbinols at 160 ° with polyphosphoric acid also promotes rearrangement.